(3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

Base Information

Chemical Name:(3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
CAS No.:87727-92-2
Molecular Formula:C₂₁H₃₆O₃Si
Molecular Weight:364.601
Hs Code.:

Synonyms:(3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

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Chemical Property of (3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

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Technology Process of (3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

There total 1 articles about (3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 26054-46-6
(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 87727-92-2
(3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: NBS / CCl₄ / 0.75 h / Heating; Irradiation

2: 76 percent / K₂CO₃ / diethyl ether

3: 34 percent / CH₂Cl₂ / -78 °C

With N-Bromosuccinimide; potassium carbonate; In tetrachloromethane; diethyl ether; dichloromethane;

Reference yield:

: 87727-92-2
(3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

: 587869-87-2
(5Z)-7-{(1RS,2SR,5RS)-2-[(1E,3SR)-3-(tert-butyldimethylsilanyloxy)oct-1-enyl]-5-(2-nitrophenylselanyl)cyclopent-3-enyl}hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: DIBAL-H / hexane; CH₂Cl₂ / 0.75 h / -78 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / 20 °C

2.2: 84 percent / tetrahydrofuran / 1 h / 20 °C

3.1: 90 percent / diethyl ether / cooling

4.1: 80 percent / nBu₃P / tetrahydrofuran / 1.5 h / 20 °C

With tributylphosphine; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo034502h

Reference yield:

: 72957-88-1,74364-95-7,74365-00-7,75800-98-5,75801-00-2,87727-92-2
6-exo-(3'-t-butyldimethylsilyloxyoct-1'-enyl)-2-oxabicyclo<3.3.0>oct-7-en-3-one

: 37517-79-6
PGA₂

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / di-isobutylaluminium hydride / petroleum ether; hexane / 0.33 h / -78 °C

2: 69 percent / potassium-t-butoxide / 3 h

3: 70 percent / chromium trioxide-dipyridinium complex / CH₂Cl₂ / 0.5 h

4: aq. acetic acid / tetrahydrofuran / 18 h

With diisobutylaluminum hydride; 2,2'-bipyridine-chromium(VI) oxide; potassium tert-butylate; acetic acid; In tetrahydrofuran; hexane; dichloromethane; Petroleum ether;